Everything about Skatole totally explained
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Skatole or
3-methylindole is a mildly
toxic white crystalline
organic compound belonging to the
indole family. It occurs naturally in
feces (it is produced from
tryptophan in the mammalian digestive tract),
beets, and
coal tar, and has a strong fecal
odor. In low
concentrations it has a
flowery smell and is found in several
flowers and
essential oils, including those of
orange blossoms,
jasmine, and
Ziziphus mauritiana. It is used as a fragrance and
fixative in many
perfumes and as an
aroma compound. Its name is derived from the Greek root
skato- meaning "
dung".
Skatole has been shown to cause
pulmonary edema in goats, sheep, rats, and some strains of mice. It appears to selectively target
Clara cells, which are the major site of
cytochrome P450 enzymes in the lungs. These enzymes convert skatole to a reactive intermediate, 3-methyleneindolenine, which damages cells by forming protein
adducts.
Skatole can be found as a white crystalline or fine powder solid, and it browns upon aging. It is nitrogenous and one of the rings is a
pyrrole. It is soluble in alcohol and
benzene and it gives violet color in potassium ferrocyanide (
K4Fe(
CN)
6·3
H2O) and
sulfuric acid (
H2SO4). Skatole has a double ring system which displays
aromaticity. It is continuous (all atoms in the ring are sp² hybridized), planar, and follows the 4n+2 rule because it has 10 π electrons. It can be synthesized through a
Fischer indole synthesis which was developed by
Emil Fischer.
It is one of many compounds that's attractive to males of various species of
orchid bees, who apparently gather the chemical to synthesize pheromones; it's commonly used as bait to attract and collect these bees for study.
In a 1994 report released by five top
cigarette companies, skatole was listed as one of the 599 additives to cigarettes.
It is a flavoring ingredient.
Further Information
Get more info on 'Skatole'.
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